2-(Dimethylamino)ethanol → Methyl 6-(benzenesulphonylmethyl)-2-(2-dimethylaminoethoxy)-3-(furan-3-yl)benzoate

HRID 2177699Notes

Reaction equation

HRID 2177699 reaction equation
[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([OH:21])[C:14]([C:22]3[CH:26]=[CH:25][O:24][CH:23]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:27][N:28]([CH3:32])[CH2:29][CH2:30]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([O:21][CH2:30][CH2:29][N:28]([CH3:32])[CH3:27])[C:14]([C:22]3[CH:26]=[CH:25][O:24][CH:23]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 79022-(Dimethylamino)ethanolHCID 11776Triphenylphosphine2×HCID 75555Diisopropyl diazene-1,2-dicarboxylate2×HCID 67107618Methyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-hydroxybenzoate2×

Product 1

HCID 67107506Methyl 6-(benzenesulphonylmethyl)-2-(2-dimethylaminoethoxy)-3-(furan-3-yl)benzoateYield 73.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of methyl 6-(benzenesulphonylmethyl)-3-(furan-3-yl)-2-hydroxybenzoate (Intermediate 114, 0.08 g), N,N-dimethylethanolamine (0.024 g) and triphenylphosphine (0.085 g) in dry THF (1 ml) was stirred and cooled to 0° C. A solution of di-isopropyl azodicarboxylate (0.065 g) in dry THF (1 ml) was added dropwise. The resultant mixture was stirred at 0° C. for 10 minutes then at room temperature overnight. Further triphenylphosphine (0.028 g) and di-isopropyl azodicarboxylate (0.022 g) was added and the mixture was stirred at room temperature for 1.5 hours then left to stand at room temperature overnight. The mixture was added to a SCX-2 column and eluted with acetonitrile followed by 2M ammonia in methanol. After evaporation of the basic eluent, the residue was repurified using an SCX-2 column, eluting with methanol followed by 2M ammonia in methanol to give methyl 6-(benzenesulphonylmethyl)-2-(2-dimethylaminoethoxy)-3-(furan-3-yl)benzoate (0.07 g) as a gum.

Workup

  1. customat room temperature
  2. customovernight
  3. stirringthe mixture was stirred at room temperature for 1.5 hours
  4. waitthen left
  5. additionThe mixture was added to a SCX-2 column
  6. washeluted with acetonitrile
  7. customAfter evaporation of the basic eluent
  8. customthe residue was repurified
  9. washeluting with methanol

Sources & evidence

ORD record
ord-458db8bd10c9423d9454cfcd75bc76d5
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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